This invention concerns the microbiological oxidation of biphenyl to 2,5-dihydroxybiphenyl(phenylhydroquinone) employing the fungus Thamnostylum piriforme (including species formerly known as Helicostylum piriforme).
Microbiological oxidation of biphenyls by a variety of bacteria and fungi has been studied. For instance:
U.S. Pat. No. 4,153,509 and Schwartz et al., Appl. Environ. Microbiol., 39, pages 702 to 708 (1980) disclose the microbiological oxidation of a biphenyl compound with a microorganism of the genus Absidia and certain species of Aspergillus and Cunninghamella. Products obtained are mono- and dihydroxybiphenyls which contain a hydroxyl group in each ring, e.g., 4-hydroxybiphenyl and 4,4'-dihydroxybiphenyl.
Japanese Application No. 54-151195 discloses a process for the preparation of p-phenylphenol and m-phenylphenol by microbiological oxidation of biphenyl by the bacterium, Pseudomonas.
Herber et al., C. R. Soc. Biol., 163, pages 1657 to 1661 (1969), disclose metabolism of 2-hydroxybiphenyl (o-phenylphenol) and its conversion to a mixture of polyhydroxyl biphenyls including 2,5-dihydroxybiphenyl by a fungus, Mucor.
Dodge et al., Biochem J., 178, pages 223 to 230 (1979), disclose formation of 2,5-dihydroxybiphenyl by microbiological oxidation of 2-hydroxybiphenyl by the fungus Cunninghamella elegans. The compound, 2,5-dihydroxybiphenyl was not obtained directly from biphenyl.
Herber et al., Chem. Abstracts, 79, 666c (1973), disclose the metabolic conversion of thymol and carvacrol into thymohydroquinone, and the conversion of 2-hydroxybiphenyl into 2,5-dihydroxybiphenyl by Mucor hiemalis.
Smith et al., Arch. Biochem. Biophys., 161, pages 551 to 558 (1974), disclose aromatic hydroxylation of biphenyl to 2-hydroxybiphenyl and 4-hydroxybiphenyl by Helicostylum piriforme.
Smith et al., J. Appl. Bacteriol., 49, pages 65 to 73 (1980), disclose use of Heliocostylum piriforme to produce 2-hydroxybiphenyl. Aspergillus niger and Cunninghamella echinulata were reported to give small amounts of 2,5-dihydroxybiphenyl in addition to major amounts of other hydroxylated products.
Kieslich, "Microbial Transformations of Non-Steroid Cyclic Compounds," John Wiley & Sons, 1976, page 512, discloses microbial transformation of biphenyl to hydroxylated biphenyls including 2,3-dihydroxybiphenyl using the bacterium Pseudomonas putida and an unspecified gram negative bacterium.